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Thermally Induced Cyclobutenone Rearrangements and Domino Reactions
Author(s) -
Harrowven David C.,
Pascoe David D.,
Guy Ian L.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200603538
Subject(s) - domino , thermal decomposition , hydroquinone , substituent , alkene , chemistry , decomposition , cyclopentenone , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Four thermal‐rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron‐rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione.
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